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In the title compound, C18H19IO7, the two aromatic rings are nearly perpendicular to each other with a dihedral angle of 83.0 (4)°. One methoxy group is twisted out of the plane of its attached benzene ring, while another methoxy group and the carbo­methoxy group are almost coplanar with their attached benzene rings. The hydroxyl groups are involved in intramolecular O—H...O hydrogen bonds with the carbomethoxy O atoms. The crystal structure is stabilized by intramolecular O—H...O hydrogen bonds and weak C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016774/na6103sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016774/na6103Isup2.hkl
Contains datablock I

CCDC reference: 176013

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.011 Å
  • Disorder in main residue
  • R factor = 0.088
  • wR factor = 0.226
  • Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??)
Author response: There is no isolated hydrogen atom.
PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      
Author response: There is no isolated hydrogen atom.
PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      
Author response: There is no isolated hydrogen atom.

Yellow Alert Alert Level C:
PLAT_301 Alert C Main Residue Disorder ........................ 7.00 Perc.
3 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The diphenyl ethers could be prepared readily by the convertion of p-depsides which are produced from a wide variety of metabolites of lichen (Elix et al., 1978) and by synthesis (Elix & Jenie, 1989; Chantrapromma et al., 1998) via an intramolecular Smiles rearrangement (Elix et al., 1984). Suitable reaction conditions for an intramolecular Smiles rearrangement of the prepared depsides have also been studied extensively (Elix & Jenie, 1989; Elix et al., 1990). In previous work, we have reported the structure of diphenyl ethers by intramolecular Smiles rearrangement of the prepared corresponding depsides (Chantrapromma et al., 2000; Karalai et al., 2001). Structure determinations were undertaken as part of our structural studies on diphenyl ether derivatives. The title compound, (I), was unexpectedly obtained upon treatment of methyl 4-(2-carboxy-3,5-methoxy-6-methylphenoxy)-2,6-dihydroxy-3-methylbenzoate with excess of methyl lithium (freshly prepared from methyl iodide and lithium), instead of the expected product, the 2-acetylphenoxy analog of the starting material. It is quite hard to get a good quality crystal of the title compound.

A displacement ellipsoid plot with the atomic numbering scheme of the title compound is shown in Fig. 1. The observed molecule is disordered into two conformations, one related to the other by rotation of the 2,6-dihydroxy-3-iodo-5-methylbenzoate moiety about the O—C central bond joining it to the phenoxy residue, by 180°. Disorder is such as to have only 3- and 5-positions of phenyl occupied alternatively by the iodine and methyl group. The bond lengths and angles observed in the structure are normal and agree with reported values (Allen et al., 1987; Chantrapromma et al., 1998, 2000; Karalai et al., 2001). The two benzene rings are nearly perpendicular to each other [dihedral angle 83.0 (4)°]. One methoxy group is coplanar with the attached benzene ring [C17—O7—C4—C3 = -0.5 (13)°] but the other is twisted out of the benzene ring [C15—O6—C2—C3 = 16.6 (12)°], while the carbomethoxy group is nearly coplanar with the attached benzene rings [C16—O2—C13—C10 = 174.2 (3)°]. The hydroxyl groups in the molecule are involved in intramolecular O—H···O hydrogen bonds with the carbomethoxy O atoms (Table 2), whereas the O atom of methoxy group is involved in a weak intramolecular C14—H14A···O7 interaction (H14A···O7 = 2.32 Å and C14—H14A···O7 = 106°). The crystal structure is stabilized by these intramolecular O—H···O hydrogen bonds and weak C—H···O interactions. The molecules are stacked on top of one another along the a axis (Fig. 2).

Experimental top

A solution of 0.98 M methyl lithium (1.10 ml, 0.99 mmol), which was freshly prepared from methyl iodide and lithium, was added to a cool solution of methyl 4-(2-carboxy-3,5-methoxy-6-methylphenoxy)-2,6-dihydroxy-3-methylbenzoate (39 mg, 0.01 mmol) in dry tetrahydrofuran (5 ml) under a nitrogen atmosphere. The reaction mixture was stirred at 273 K for 3 h and an for an additional 6 h at room temperature. Saturated ammonium chloride (30 ml) was then added to the solution. The resulting mixture was extracted with ether. After extraction, the solvent was removed in vacuo and the crude product was purified by preparative thin-layer chromatography with 20% hexane/chloroform as eluent to give a brown solid which was recrystallized from chloroform.

Refinement top

After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on the atoms to which they were attached, with Uiso = 1.2Ueq for aromatic parent atoms and 1.5Ueq for methyl C atoms and hydroxyl O atoms, and with –C–H = 0.96 Å and O—H = 0.82 Å. Due to a large fraction of weak data at higher angles, the 2θ maximum was limited to 50°. Even with this limitation, the coverage of the unit set is only 93.2% complete because the crystal is not very reflecting and there is disorder in the structure.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. I/CA is the I atom for conformation A where as I/CB is the I atom for conformation B.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the a axis. Only conformation A is shown to avoid confusion.
Methyl 4-(3,5-dimethoxy-2-methylphenoxy)-2,6-dihydroxy-3-iodo-5-methylbenzoate top
Crystal data top
C18H19IO7Z = 2
Mr = 474.23F(000) = 472
Triclinic, P1Dx = 1.688 Mg m3
a = 8.8878 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6008 (2) ÅCell parameters from 3302 reflections
c = 11.2792 (3) Åθ = 2.0–25.0°
α = 62.253 (1)°µ = 1.75 mm1
β = 87.872 (1)°T = 293 K
γ = 82.953 (1)°Block, brown
V = 933.16 (4) Å30.36 × 0.24 × 0.18 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3302 independent reflections
Radiation source: fine-focus sealed tube2039 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.0°
ω scansh = 710
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1012
Tmin = 0.571, Tmax = 0.743l = 1013
5044 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.088H-atom parameters constrained
wR(F2) = 0.226 w = 1/[σ2(Fo2) + (0.1141P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
3078 reflectionsΔρmax = 1.46 e Å3
250 parametersΔρmin = 0.65 e Å3
4 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.098 (11)
Crystal data top
C18H19IO7γ = 82.953 (1)°
Mr = 474.23V = 933.16 (4) Å3
Triclinic, P1Z = 2
a = 8.8878 (3) ÅMo Kα radiation
b = 10.6008 (2) ŵ = 1.75 mm1
c = 11.2792 (3) ÅT = 293 K
α = 62.253 (1)°0.36 × 0.24 × 0.18 mm
β = 87.872 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
3302 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2039 reflections with I > 2σ(I)
Tmin = 0.571, Tmax = 0.743Rint = 0.081
5044 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0884 restraints
wR(F2) = 0.226H-atom parameters constrained
S = 0.98Δρmax = 1.46 e Å3
3078 reflectionsΔρmin = 0.65 e Å3
250 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0,88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4.023 cm and the detector swing angle was -35°. Crystal decay was monitored by SAINT (Siemens, 1996) and was found to be negligible.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I/CA0.95733 (11)0.34053 (11)0.19968 (10)0.0688 (5)0.569 (4)
C18A1.349 (3)0.115 (2)0.235 (2)0.0658 (6)0.569 (4)
H18A1.27410.12850.18410.099*0.569 (4)
H18B1.39230.20620.30360.099*0.569 (4)
H18C1.42790.06680.17590.099*0.569 (4)
I/CB1.37477 (17)0.13760 (17)0.20670 (16)0.0658 (6)0.43
C18B1.023 (3)0.3084 (18)0.210 (2)0.0688 (5)0.43
H18E0.95800.33710.26480.103*0.431 (4)
H18F0.96290.30150.14450.103*0.431 (4)
H18G1.09220.37830.16470.103*0.431 (4)
O11.1253 (6)0.1309 (6)0.1016 (5)0.0604 (15)
O21.2331 (6)0.0068 (6)0.7032 (6)0.0684 (16)
O31.4130 (7)0.1511 (7)0.6924 (6)0.0780 (18)
O41.0851 (7)0.2005 (7)0.4884 (6)0.0773 (17)
H4A1.11120.16470.56750.116*
O51.4334 (7)0.1871 (6)0.4849 (6)0.0739 (17)
H5A1.45270.20140.56100.111*
O61.5512 (6)0.3868 (6)0.0681 (6)0.0685 (16)
O71.1531 (7)0.4092 (7)0.3599 (5)0.0795 (19)
C11.3417 (8)0.2638 (8)0.0172 (7)0.0517 (17)
H1A1.38170.22790.10340.062*
C21.4172 (8)0.3582 (8)0.0945 (7)0.0509 (18)
C31.3561 (8)0.4090 (7)0.2229 (6)0.054 (2)
H3A1.40550.47140.29760.065*
C41.2222 (8)0.3654 (8)0.2373 (7)0.0507 (18)
C51.1380 (8)0.2728 (8)0.1283 (7)0.0524 (18)
C61.2067 (8)0.2257 (7)0.0042 (7)0.0490 (17)
C71.1746 (8)0.0907 (8)0.2352 (7)0.0548 (19)
C81.1092 (8)0.1682 (7)0.2937 (7)0.058 (2)
C91.1534 (9)0.1181 (9)0.4334 (8)0.0570 (19)
C101.2600 (8)0.0017 (8)0.4966 (7)0.0520 (18)
C111.3229 (8)0.0736 (8)0.4274 (8)0.0520 (18)
C121.2794 (8)0.0278 (7)0.2948 (6)0.0534 (18)
C131.3094 (9)0.0567 (9)0.6404 (8)0.060 (2)
C140.9917 (9)0.2348 (9)0.1461 (8)0.067 (2)
H14A0.98020.25220.23690.100*
H14B0.91220.29220.12690.100*
H14C0.98620.13510.08630.100*
C151.6214 (10)0.5009 (9)0.1677 (9)0.068 (2)
H15A1.70930.51430.13000.102*
H15B1.55150.58720.20180.102*
H15C1.65110.47890.23940.102*
C161.2671 (12)0.0555 (12)0.8457 (9)0.083 (3)
H16A1.20680.00110.88240.125*
H16B1.37270.05360.85910.125*
H16C1.24430.15300.88970.125*
C171.2270 (12)0.5081 (15)0.4799 (9)0.105 (4)
H17A1.17520.52010.55830.157*
H17B1.33080.46960.47930.157*
H17C1.22360.59940.48080.157*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I/CA0.0664 (8)0.0533 (7)0.0610 (7)0.0064 (4)0.0118 (5)0.0072 (4)
C18A0.0814 (11)0.0652 (9)0.0658 (10)0.0207 (7)0.0150 (7)0.0413 (7)
I/CB0.0814 (11)0.0652 (9)0.0658 (10)0.0207 (7)0.0150 (7)0.0413 (7)
C18B0.0664 (8)0.0533 (7)0.0610 (7)0.0064 (4)0.0118 (5)0.0072 (4)
O10.060 (3)0.074 (3)0.029 (3)0.028 (3)0.001 (2)0.004 (2)
O20.080 (4)0.071 (4)0.042 (3)0.008 (3)0.003 (2)0.016 (3)
O30.089 (4)0.073 (4)0.046 (3)0.004 (3)0.008 (3)0.006 (3)
O40.096 (4)0.079 (4)0.053 (4)0.016 (3)0.009 (3)0.033 (3)
O50.087 (4)0.053 (3)0.058 (4)0.006 (3)0.014 (3)0.008 (3)
O60.066 (4)0.063 (4)0.055 (3)0.023 (3)0.007 (2)0.006 (3)
O70.085 (4)0.099 (5)0.023 (3)0.023 (3)0.003 (2)0.001 (3)
C10.064 (5)0.048 (4)0.032 (4)0.011 (3)0.004 (3)0.008 (3)
C20.040 (4)0.055 (4)0.047 (4)0.014 (3)0.004 (3)0.013 (3)
C30.066 (5)0.052 (4)0.025 (3)0.005 (3)0.008 (3)0.003 (3)
C40.050 (4)0.054 (4)0.034 (4)0.010 (3)0.001 (3)0.007 (3)
C50.053 (4)0.050 (4)0.042 (4)0.005 (3)0.003 (3)0.012 (3)
C60.056 (5)0.042 (4)0.031 (3)0.012 (3)0.002 (3)0.001 (3)
C70.062 (5)0.057 (5)0.033 (4)0.027 (4)0.000 (3)0.005 (3)
C80.065 (5)0.052 (4)0.040 (4)0.011 (3)0.001 (3)0.007 (3)
C90.064 (5)0.060 (5)0.043 (4)0.011 (4)0.001 (3)0.018 (3)
C100.056 (4)0.050 (4)0.032 (4)0.018 (3)0.002 (3)0.002 (3)
C110.044 (4)0.049 (4)0.055 (5)0.008 (3)0.001 (3)0.017 (3)
C120.064 (5)0.052 (4)0.030 (4)0.017 (3)0.005 (3)0.005 (3)
C130.061 (5)0.058 (5)0.043 (4)0.014 (4)0.001 (3)0.008 (4)
C140.070 (5)0.066 (5)0.044 (4)0.018 (4)0.004 (3)0.006 (3)
C150.073 (5)0.057 (5)0.064 (5)0.035 (4)0.020 (4)0.015 (4)
C160.088 (7)0.097 (7)0.043 (5)0.013 (5)0.006 (4)0.014 (4)
C170.104 (8)0.154 (11)0.033 (5)0.055 (7)0.007 (4)0.014 (5)
Geometric parameters (Å, º) top
I/CA—C81.995 (6)C2—C31.394 (10)
C18A—C121.452 (9)C3—C41.369 (10)
C18A—H18A0.9600C3—H3A0.9300
C18A—H18B0.9600C4—C51.422 (10)
C18A—H18C0.9600C5—C61.385 (10)
I/CB—C121.958 (6)C5—C141.455 (11)
C18B—C81.468 (10)C7—C81.345 (11)
C18B—H18E0.9600C7—C121.368 (10)
C18B—H18F0.9600C8—C91.461 (11)
C18B—H18G0.9600C9—C101.368 (11)
O1—C61.398 (8)C10—C111.414 (11)
O1—C71.431 (8)C10—C131.503 (10)
O2—C131.308 (10)C11—C121.394 (10)
O2—C161.452 (10)C14—H14A0.9600
O3—C131.209 (10)C14—H14B0.9600
O4—C91.365 (10)C14—H14C0.9600
O4—H4A0.8200C15—H15A0.9600
O5—C111.365 (9)C15—H15B0.9600
O5—H5A0.8200C15—H15C0.9600
O6—C21.341 (9)C16—H16A0.9600
O6—C151.407 (9)C16—H16B0.9600
O7—C41.379 (9)C16—H16C0.9600
O7—C171.465 (11)C17—H17A0.9600
C1—C61.376 (10)C17—H17B0.9600
C1—C21.402 (10)C17—H17C0.9600
C1—H1A0.9300
C12—C18A—H18A109.5O4—C9—C10125.2 (7)
C12—C18A—H18B109.5O4—C9—C8114.2 (7)
C12—C18A—H18C109.5C10—C9—C8120.5 (7)
C8—C18B—H18E109.5C9—C10—C11119.5 (7)
C8—C18B—H18F109.5C9—C10—C13123.3 (7)
H18E—C18B—H18F109.5C11—C10—C13117.2 (7)
C8—C18B—H18G109.5O5—C11—C12118.2 (7)
H18E—C18B—H18G109.5O5—C11—C10121.4 (7)
H18F—C18B—H18G109.5C12—C11—C10120.3 (6)
C6—O1—C7117.7 (5)C7—C12—C11118.0 (6)
C13—O2—C16115.6 (7)C7—C12—C18A126.4 (12)
C9—O4—H4A109.5C11—C12—C18A115.5 (12)
C11—O5—H5A109.5C7—C12—I/CB124.7 (5)
C2—O6—C15119.9 (6)C11—C12—I/CB117.3 (5)
C4—O7—C17117.8 (7)C18A—C12—I/CB2.4 (10)
C6—C1—C2118.2 (6)O3—C13—O2123.0 (8)
C6—C1—H1A120.9O3—C13—C10123.0 (8)
C2—C1—H1A120.9O2—C13—C10113.9 (7)
O6—C2—C3124.4 (6)C5—C14—H14A109.5
O6—C2—C1115.6 (7)C5—C14—H14B109.5
C3—C2—C1119.9 (7)H14A—C14—H14B109.5
C4—C3—C2118.9 (6)C5—C14—H14C109.5
C4—C3—H3A120.5H14A—C14—H14C109.5
C2—C3—H3A120.5H14B—C14—H14C109.5
C3—C4—O7123.3 (6)O6—C15—H15A109.5
C3—C4—C5124.0 (7)O6—C15—H15B109.5
O7—C4—C5112.7 (7)H15A—C15—H15B109.5
C6—C5—C4113.6 (7)O6—C15—H15C109.5
C6—C5—C14123.5 (7)H15A—C15—H15C109.5
C4—C5—C14122.9 (7)H15B—C15—H15C109.5
C1—C6—C5125.3 (6)O2—C16—H16A109.5
C1—C6—O1121.7 (6)O2—C16—H16B109.5
C5—C6—O1113.0 (6)H16A—C16—H16B109.5
C8—C7—C12125.5 (7)O2—C16—H16C109.5
C8—C7—O1117.5 (7)H16A—C16—H16C109.5
C12—C7—O1117.0 (7)H16B—C16—H16C109.5
C7—C8—C9116.2 (6)O7—C17—H17A109.5
C7—C8—C18B118.9 (13)O7—C17—H17B109.5
C9—C8—C18B123.9 (13)H17A—C17—H17B109.5
C7—C8—I/CA123.1 (6)O7—C17—H17C109.5
C9—C8—I/CA120.7 (6)H17A—C17—H17C109.5
C18B—C8—I/CA11.3 (11)H17B—C17—H17C109.5
C15—O6—C2—C316.6 (12)C18B—C8—C9—O411.4 (17)
C15—O6—C2—C1167.2 (7)I/CA—C8—C9—O41.4 (9)
C6—C1—C2—O6177.3 (6)C7—C8—C9—C102.4 (11)
C6—C1—C2—C30.9 (11)C18B—C8—C9—C10165.8 (15)
O6—C2—C3—C4176.2 (7)I/CA—C8—C9—C10178.6 (6)
C1—C2—C3—C40.2 (11)O4—C9—C10—C11179.4 (7)
C2—C3—C4—O7179.8 (7)C8—C9—C10—C112.6 (11)
C2—C3—C4—C51.5 (11)O4—C9—C10—C133.9 (12)
C17—O7—C4—C30.5 (13)C8—C9—C10—C13179.2 (7)
C17—O7—C4—C5178.4 (9)C9—C10—C11—O5177.6 (7)
C3—C4—C5—C62.1 (11)C13—C10—C11—O55.5 (10)
O7—C4—C5—C6179.0 (7)C9—C10—C11—C121.5 (11)
C3—C4—C5—C14176.4 (8)C13—C10—C11—C12178.4 (7)
O7—C4—C5—C142.5 (11)C8—C7—C12—C110.2 (11)
C2—C1—C6—C50.1 (12)O1—C7—C12—C11176.5 (6)
C2—C1—C6—O1179.3 (7)C8—C7—C12—C18A178.7 (13)
C4—C5—C6—C11.3 (11)O1—C7—C12—C18A2.0 (15)
C14—C5—C6—C1177.2 (8)C8—C7—C12—I/CB179.3 (6)
C4—C5—C6—O1177.9 (6)O1—C7—C12—I/CB4.0 (9)
C14—C5—C6—O13.6 (11)O5—C11—C12—C7176.5 (7)
C7—O1—C6—C19.1 (11)C10—C11—C12—C70.3 (10)
C7—O1—C6—C5171.7 (7)O5—C11—C12—C18A4.8 (14)
C6—O1—C7—C893.2 (8)C10—C11—C12—C18A179.0 (12)
C6—O1—C7—C1289.8 (8)O5—C11—C12—I/CB3.0 (9)
C12—C7—C8—C91.2 (11)C10—C11—C12—I/CB179.2 (5)
O1—C7—C8—C9175.5 (6)C16—O2—C13—O37.7 (12)
C12—C7—C8—C18B167.6 (14)C16—O2—C13—C10174.2 (7)
O1—C7—C8—C18B15.7 (16)C9—C10—C13—O3173.1 (8)
C12—C7—C8—I/CA179.8 (6)C11—C10—C13—O310.2 (11)
O1—C7—C8—I/CA3.5 (9)C9—C10—C13—O25.0 (11)
C7—C8—C9—O4179.6 (7)C11—C10—C13—O2171.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O20.821.902.600 (9)143
O5—H5A···O30.821.802.538 (9)148

Experimental details

Crystal data
Chemical formulaC18H19IO7
Mr474.23
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.8878 (3), 10.6008 (2), 11.2792 (3)
α, β, γ (°)62.253 (1), 87.872 (1), 82.953 (1)
V3)933.16 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.75
Crystal size (mm)0.36 × 0.24 × 0.18
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.571, 0.743
No. of measured, independent and
observed [I > 2σ(I)] reflections
5044, 3302, 2039
Rint0.081
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.088, 0.226, 0.98
No. of reflections3078
No. of parameters250
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.46, 0.65

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
I/CA—C81.995 (6)I/CB—C121.958 (6)
C18A—C121.452 (9)C18B—C81.468 (10)
C6—O1—C7117.7 (5)
C15—O6—C2—C316.6 (12)C8—C7—C12—C18A178.7 (13)
C6—C1—C2—O6177.3 (6)C8—C7—C12—I/CB179.3 (6)
C14—C5—C6—C1177.2 (8)C16—O2—C13—C10174.2 (7)
I/CA—C8—C9—C10178.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O20.821.902.600 (9)143
O5—H5A···O30.821.802.538 (9)148
 

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